data_global
_journal_name_full               Phys.Chem.Chem.Phys.(PCCP)

_journal_coden_Cambridge         1326

_publ_contact_author_name        'Rasmussen, Seth'
_publ_contact_author_email       seth.rasmussen@ndsu.edu

_publ_section_title              
;
Solution and Solid-state Properties of Highly Fluorescent
Dithieno[3,2-b:2',3'-d]pyrrole-based Oligothiophenes
;
loop_
_publ_author_name
H.Mo
K.Radke
K.Ogawa
C.Heth
B.Erpelding
S.Rasmussen

# Attachment '- tBuDTPoligomer 041907.cif'

data_ta
_database_code_depnum_ccdc_archive 'CCDC 781843'
#TrackingRef '- tBuDTPoligomer 041907.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N-tert-Butyl-2,6-bis(2'-thienyl)dithieno[3,2-b:2',3'-d]pyrrole
;
_chemical_name_common            
N-tert-Butyl-2,6-bis(2'-thienyl)dithieno(3,2-b:2',3'-d)pyrrole
_chemical_melting_point          168
_chemical_formula_moiety         'C20 H17 N S4'
_chemical_formula_sum            'C20 H17 N S4'
_chemical_formula_weight         399.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.489(4)
_cell_length_b                   7.8855(16)
_cell_length_c                   14.540(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.37(3)
_cell_angle_gamma                90.00
_cell_volume                     1903.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8545
_exptl_absorpt_correction_T_max  0.9051
_exptl_absorpt_process_details   'SADABS v2.03'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker 1K CCd Diffractometer'
_diffrn_measurement_method       'Phi plus Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37314
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_sigmaI/netI    0.0759
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4247
_reflns_number_gt                2227
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0345P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4247
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.10825(4) 0.67188(6) 0.30995(4) 0.05199(19) Uani 1 1 d . C .
S2 S 0.27163(4) 0.71890(7) 0.58055(4) 0.05534(19) Uani 1 1 d . C .
N1 N 0.25858(10) 1.04091(19) 0.37908(12) 0.0455(4) Uani 1 1 d . C .
C1 C -0.04123(16) 0.7129(3) -0.04759(19) 0.0665(7) Uani 1 1 d . . .
H1A H -0.0571 0.7115 -0.1149 0.080 Uiso 1 1 calc R A 1
C2 C -0.08768(16) 0.6477(3) 0.00110(19) 0.0721(8) Uani 1 1 d . C .
H2A H -0.1372 0.5981 -0.0308 0.087 Uiso 1 1 calc R B 1
S3 S 0.04197(7) 0.79279(13) 0.01488(8) 0.0692(6) Uani 0.448(9) 1 d P C 1
C3 C -0.05386(6) 0.65909(13) 0.11713(8) 0.0772(6) Uani 0.45(2) 1 d P C 1
H3A H -0.0741 0.6238 0.1660 0.093 Uiso 0.45(2) 1 calc PR C 1
S3' S -0.05386(6) 0.65909(13) 0.11713(8) 0.0772(6) Uani 0.552(9) 1 d P C 2
C3' C 0.04197(7) 0.79279(13) 0.01488(8) 0.0692(6) Uani 0.55(2) 1 d P C 2
H3'A H 0.0836 0.8435 -0.0022 0.083 Uiso 0.55(2) 1 calc PR C 2
C4 C 0.02956(13) 0.7559(2) 0.11795(15) 0.0455(5) Uani 1 1 d . . .
C5 C 0.09160(12) 0.8025(2) 0.20873(15) 0.0422(5) Uani 1 1 d . C .
C6 C 0.14249(12) 0.9375(2) 0.22517(14) 0.0437(5) Uani 1 1 d . . .
H6A H 0.1421 1.0191 0.1788 0.052 Uiso 1 1 calc R C .
C7 C 0.19625(12) 0.9391(2) 0.32139(14) 0.0401(5) Uani 1 1 d . C .
C8 C 0.18478(12) 0.8020(2) 0.37610(15) 0.0421(5) Uani 1 1 d . . .
C9 C 0.24103(12) 0.8175(2) 0.46929(15) 0.0431(5) Uani 1 1 d . C .
C10 C 0.28575(12) 0.9636(2) 0.46947(15) 0.0409(5) Uani 1 1 d . . .
C11 C 0.34438(12) 0.9962(2) 0.56016(15) 0.0466(5) Uani 1 1 d . C .
H11A H 0.3790 1.0888 0.5724 0.056 Uiso 1 1 calc R . .
C12 C 0.34412(12) 0.8759(2) 0.62749(15) 0.0437(5) Uani 1 1 d . . .
C13 C 0.39412(12) 0.8672(2) 0.72828(15) 0.0448(5) Uani 1 1 d . C .
S4 S 0.48534(4) 0.96003(9) 0.76746(6) 0.0578(4) Uani 0.748(8) 1 d P C 1
C14 C 0.37290(10) 0.77894(18) 0.80790(11) 0.0658(8) Uani 0.71(2) 1 d P C 1
H14A H 0.3263 0.7183 0.8036 0.079 Uiso 0.71(2) 1 calc PR C 1
S4' S 0.37290(10) 0.77894(18) 0.80790(11) 0.0658(8) Uani 0.252(8) 1 d P C 2
C14' C 0.48534(4) 0.96003(9) 0.76746(6) 0.0578(4) Uani 0.29(2) 1 d P C 2
H14B H 0.5154 1.0218 0.7365 0.069 Uiso 0.29(2) 1 calc PR C 2
C15 C 0.44207(17) 0.8096(3) 0.89413(18) 0.0683(7) Uani 1 1 d . . .
H15A H 0.4442 0.7676 0.9547 0.082 Uiso 1 1 calc R C 1
C16 C 0.50173(15) 0.9011(3) 0.88105(18) 0.0691(7) Uani 1 1 d . C .
H16A H 0.5482 0.9291 0.9310 0.083 Uiso 1 1 calc R D 1
C17 C 0.28988(14) 1.2067(2) 0.35584(17) 0.0553(6) Uani 1 1 d . . .
C18 C 0.37984(16) 1.1885(3) 0.3719(2) 0.0779(8) Uani 1 1 d . C .
H18A H 0.3885 1.1050 0.3282 0.117 Uiso 1 1 calc R . .
H18B H 0.4064 1.1536 0.4375 0.117 Uiso 1 1 calc R . .
H18C H 0.4014 1.2954 0.3603 0.117 Uiso 1 1 calc R . .
C19 C 0.27518(15) 1.3415(2) 0.42484(18) 0.0705(8) Uani 1 1 d . C .
H19A H 0.2183 1.3533 0.4137 0.106 Uiso 1 1 calc R . .
H19B H 0.2970 1.4482 0.4132 0.106 Uiso 1 1 calc R . .
H19C H 0.3011 1.3073 0.4907 0.106 Uiso 1 1 calc R . .
C20 C 0.24653(19) 1.2586(3) 0.25300(19) 0.0979(11) Uani 1 1 d . C .
H20A H 0.2559 1.1756 0.2094 0.147 Uiso 1 1 calc R . .
H20B H 0.2663 1.3668 0.2403 0.147 Uiso 1 1 calc R . .
H20C H 0.1898 1.2664 0.2436 0.147 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0567(4) 0.0492(3) 0.0454(4) -0.0003(3) 0.0094(3) -0.0161(3)
S2 0.0625(4) 0.0493(3) 0.0461(4) 0.0044(3) 0.0054(3) -0.0120(3)
N1 0.0514(11) 0.0405(9) 0.0405(11) 0.0002(8) 0.0087(9) -0.0130(8)
C1 0.0654(18) 0.0671(15) 0.0521(16) -0.0029(13) -0.0029(14) 0.0014(13)
C2 0.0571(17) 0.0729(17) 0.073(2) -0.0103(14) 0.0015(15) -0.0131(13)
S3 0.0753(10) 0.0719(8) 0.0480(8) -0.0085(5) 0.0018(6) -0.0066(6)
C3 0.0628(8) 0.0935(9) 0.0682(9) -0.0089(6) 0.0103(6) -0.0219(6)
S3' 0.0628(8) 0.0935(9) 0.0682(9) -0.0089(6) 0.0103(6) -0.0219(6)
C3' 0.0753(10) 0.0719(8) 0.0480(8) -0.0085(5) 0.0018(6) -0.0066(6)
C4 0.0489(14) 0.0398(11) 0.0474(14) -0.0047(10) 0.0146(12) -0.0007(10)
C5 0.0442(13) 0.0420(11) 0.0414(13) -0.0042(9) 0.0149(11) -0.0025(10)
C6 0.0513(14) 0.0405(12) 0.0399(13) -0.0008(10) 0.0155(11) -0.0055(10)
C7 0.0408(13) 0.0401(11) 0.0404(13) -0.0039(10) 0.0143(11) -0.0040(10)
C8 0.0436(13) 0.0389(11) 0.0425(13) -0.0017(10) 0.0116(11) -0.0057(10)
C9 0.0433(13) 0.0419(12) 0.0427(13) -0.0010(10) 0.0115(11) -0.0029(10)
C10 0.0454(13) 0.0358(11) 0.0427(14) -0.0011(10) 0.0154(11) -0.0031(10)
C11 0.0432(13) 0.0434(12) 0.0501(14) -0.0075(11) 0.0101(11) -0.0076(10)
C12 0.0420(13) 0.0417(11) 0.0455(14) -0.0028(10) 0.0111(11) 0.0012(9)
C13 0.0440(13) 0.0415(11) 0.0447(14) -0.0061(10) 0.0080(11) 0.0055(10)
S4 0.0460(5) 0.0639(5) 0.0596(6) -0.0076(4) 0.0112(4) -0.0007(3)
C14 0.0703(13) 0.0648(11) 0.0558(11) 0.0023(8) 0.0107(9) 0.0082(8)
S4' 0.0703(13) 0.0648(11) 0.0558(11) 0.0023(8) 0.0107(9) 0.0082(8)
C14' 0.0460(5) 0.0639(5) 0.0596(6) -0.0076(4) 0.0112(4) -0.0007(3)
C15 0.083(2) 0.0661(16) 0.0481(16) 0.0057(13) 0.0101(15) 0.0118(15)
C16 0.0548(17) 0.0658(15) 0.0671(19) -0.0161(14) -0.0087(14) 0.0159(13)
C17 0.0598(16) 0.0471(13) 0.0543(16) 0.0031(11) 0.0116(13) -0.0170(11)
C18 0.080(2) 0.0706(17) 0.093(2) -0.0097(14) 0.0413(17) -0.0265(14)
C19 0.0810(19) 0.0437(13) 0.0816(19) -0.0046(13) 0.0183(16) -0.0055(12)
C20 0.126(3) 0.0819(18) 0.0628(19) 0.0244(14) -0.0024(18) -0.0566(17)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.720(2) . ?
S1 C5 1.744(2) . ?
S2 C9 1.721(2) . ?
S2 C12 1.749(2) . ?
N1 C10 1.390(2) . ?
N1 C7 1.400(2) . ?
N1 C17 1.497(2) . ?
C1 C2 1.337(3) . ?
C1 S3 1.583(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.605(3) . ?
C2 H2A 0.9300 . ?
S3 C4 1.607(2) . ?
C3 C4 1.643(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.467(3) . ?
C5 C6 1.359(3) . ?
C6 C7 1.419(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.394(3) . ?
C8 C9 1.407(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.416(3) . ?
C11 C12 1.364(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.452(3) . ?
C13 C14 1.494(3) . ?
C13 S4 1.683(2) . ?
S4 C16 1.651(3) . ?
C14 C15 1.462(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.330(3) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C20 1.504(3) . ?
C17 C18 1.523(3) . ?
C17 C19 1.538(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C5 90.77(10) . . ?
C9 S2 C12 91.12(10) . . ?
C10 N1 C7 106.54(15) . . ?
C10 N1 C17 123.80(16) . . ?
C7 N1 C17 129.56(17) . . ?
C2 C1 S3 116.8(2) . . ?
C2 C1 H1A 121.6 . . ?
S3 C1 H1A 121.6 . . ?
C1 C2 C3 116.8(2) . . ?
C1 C2 H2A 121.6 . . ?
C3 C2 H2A 121.6 . . ?
C1 S3 C4 95.35(15) . . ?
C2 C3 C4 93.79(14) . . ?
C2 C3 H3A 133.1 . . ?
C4 C3 H3A 133.1 . . ?
C5 C4 S3 120.98(17) . . ?
C5 C4 C3 121.75(17) . . ?
S3 C4 C3 117.24(14) . . ?
C6 C5 C4 127.74(19) . . ?
C6 C5 S1 112.83(16) . . ?
C4 C5 S1 119.40(14) . . ?
C5 C6 C7 111.97(18) . . ?
C5 C6 H6A 124.0 . . ?
C7 C6 H6A 124.0 . . ?
C8 C7 N1 109.14(17) . . ?
C8 C7 C6 112.71(17) . . ?
N1 C7 C6 138.14(18) . . ?
C7 C8 C9 107.42(17) . . ?
C7 C8 S1 111.72(15) . . ?
C9 C8 S1 140.86(16) . . ?
C10 C9 C8 107.22(18) . . ?
C10 C9 S2 111.35(15) . . ?
C8 C9 S2 141.43(16) . . ?
N1 C10 C9 109.68(17) . . ?
N1 C10 C11 137.13(18) . . ?
C9 C10 C11 113.17(18) . . ?
C12 C11 C10 112.16(18) . . ?
C12 C11 H11A 123.9 . . ?
C10 C11 H11A 123.9 . . ?
C11 C12 C13 128.30(18) . . ?
C11 C12 S2 112.20(16) . . ?
C13 C12 S2 119.49(15) . . ?
C12 C13 C14 125.88(18) . . ?
C12 C13 S4 121.74(17) . . ?
C14 C13 S4 112.38(14) . . ?
C16 S4 C13 93.63(13) . . ?
C15 C14 C13 104.29(17) . . ?
C15 C14 H14A 127.9 . . ?
C13 C14 H14A 127.9 . . ?
C16 C15 C14 116.2(2) . . ?
C16 C15 H15A 121.9 . . ?
C14 C15 H15A 121.9 . . ?
C15 C16 S4 113.50(19) . . ?
C15 C16 H16A 123.2 . . ?
S4 C16 H16A 123.2 . . ?
N1 C17 C20 110.87(17) . . ?
N1 C17 C18 108.45(18) . . ?
C20 C17 C18 110.6(2) . . ?
N1 C17 C19 107.96(19) . . ?
C20 C17 C19 109.0(2) . . ?
C18 C17 C19 109.99(19) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.047